


will you love me

by BabyMilk



Series: requests [25]
Category: Teen Wolf (TV)
Genre: Aftercare, Anal Sex, Blow Jobs, Body Worship, CEO Theo, Collars, College Student Stiles, Crossdressing Kink, Developing Relationship, Dirty Talk, Face Sitting, Hair Pulling, Hand Jobs, Hickies, M/M, One Shot, Panties, Rimming, Scott and Derek are good friends, Sexual Roleplay, Skirts, Spanking, Sugar Daddy Theo, Theo is a lil German, actually has a lil bit of plot, bdsm relationship, beej, brief sexting, dom!Theo, i guess, it might be a lil cheesy, sorry - Freeform, sub! Stiles, wary friends
Language: English
Status: Completed
Published: 2016-04-03
Updated: 2016-04-03
Packaged: 2018-05-30 21:29:38
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,487
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6441490
Author URL: https://archiveofourown.org/users/BabyMilk/pseuds/BabyMilk
Summary: <blockquote class="userstuff">
              <p>Things aren't going so well for Stiles Stilinski. <br/>When a handsome man offers him "work", will he take it?</p>
            </blockquote>





	will you love me

**Author's Note:**

> wowzers this took a while  
> sorry about that  
> for anon!  
> enjoy!!!

Stiles needed this, the thrumming of base in his ears and the burn of alcohol in his throat. Today had been  _ bad,  _ laid off from his third job this year Stiles Stilinski was dangerously close to losing his already shitty apartment and living on the street corner like a homeless waif. 

‘Need a refill, honey?” Erica asked, voice sympathetic and garbled from the clubs music. Stiles just nodded solemnly, staring lifelessly into the wet bottom of his empty glass. He missed Ericas concerned look. 

A freshly poured drink slid into Stiles’ periff as a stranger approached. The young man didn’t bother to look up in his depression. Erica tended to the new customer, voice sickly sweet. 

“You look like you’ve been having a hard day.” The man said, warm palm sliding across Stiles’ back “No, just - “ Stiles caught the mans eye, his dark hair and face seemed so familiar “Do I… know you?” Stiles asked. 

The man smiled charmingly “Don’t worry about that.” He said, a slight German accent curving his words “What’s bothering you?”

Stiles gave him a somewhat odd look before spilling his guts “I got fired today… My third job this year, actually. I’m finishing school, can’t hardly afford my books… I’m gonna get kicked out of my apartment…” Stiles scrubbed his hands across his face, stress radiating from his body like a chemical. 

The man gave him a sympathetic glance with a forlorn smile “I think I can help you.” 

\---

“What, like…. A hooker?”

The man released a belly deep laugh, slapping his thigh. 

Stiles had joined this stranger in his very, very pristine (fresh smelling) car in the clubs parking lot. What possessed him to do so, Stiles couldn't tell you. 

A solid minute of deep, rumbling laughter finally subsided “well.” He said, coughing with a wide grin “not necessarily. Boundaries will be all up to you.” 

Stils pondered this for a moment, hands fiddling anxiously in his lap. “I’ll let you think about it.” He slipped a firm rectangular card into Stiles’ squirming hands, dark letters printed across its surface. A business card?

Stiles nodded with a creased brow, feeling awkward and nervous. Stumbling a bit Stiles exited the mans vehicle, watching him drive off with a stifled wave. 

The dim club lights were just enough to read the small business card.

THEO RAEKEN it read, a business telephone number inked in the bottom left corner. 

“Going home, sweetheart?” Erica appeared, denim coat hugged tightly around her body for warmth “oh - uh - yeah.” He quickly fumbled the card into his back pocket, sending Erica a quick wave “i’ll call you.”

It only took one look at his apartment, the plain and cracked walls, horrific lighting, shitty “furniture”, piling unpaid bills to make his decision. 

“I need this money.”

\---

“Hello, Raekens office.” A delightful young womans voice answered the phone, startling Stiles “oh - uhm, yeah, hi, I’m calling for… Theo Raeken?” Stiles read the business card in his palm. He’d set up his station, a telephone brought from across the room to his bed, legs folded beneath him. 

Hopefully Mr. Raeken hadn’t forgotten about poor Stiles, he’d seemed nice enough.

“Alright.” The woman answered “let me put you on hold.” 

Tracy Stewart, secretary of Theo Raeken and now ex girlfriend, kept the black corded telephone wedged between her ear and shoulder, manicured finger pressing the transfer button “Theo.” she sang into the receiver.  _ “Yes, Miss Stewart?”  _ Theo replied, less fondly “You have a call. Should I send it over?” She asked, staring at her reflection from shimmering nails. “Yes, thank you.”

The line went silent for about ten seconds when a click sounded on Theos speaker.  _ “Uhm… hello?”  _ An uncertain and familiar voice came over Theo, a smile blooming on his face “hello. Whom is speaking?” 

_ “Stiles!”  _ The boy nearly shouted  _ “Stiles, uhm, from the… club.”  _ “Of course.” Theo leaned his chin on his palm “how can I help you, Stiles?” 

The boy fidgeted on his bed, eyes drawn to a fly buzzing softly on his ancient writing desk “Uhm… You had mentioned a job for me. Last night.”  _ “Mmhm.”  _ Stiles could hear the smile on Raekens face.  _ “Are you interested?”  _

“Yes.” Stiles said definitely, a fire in his heart. 

The two arranged a meeting downtown for that afternoon. At a local coffee shop, a neutral environment to discuss their ‘agreement’. 

\-----

Briefly Stiles had worried he’d missed the man. Sitting alone in a coffee shop was somewhat humiliating, especially if you didn’t have a drink or some sort of pastry to distract yourself from staring strangers. 

Stiles thrummed his fingers nervously on the plastic tables surface, checking the buildings clock every few seconds. 

Maybe he wasn’t going to show. 

About to give up for good a tell tale ring-ding sparkled through the air, the cafe door opening. “Good afternoon!” A friendly waitress greeted the customer “Hello.” 

Stiles knew that voice. Thank god, Mr Raeken! “Hello, Stiles.” Theo greeted, sliding into the booth seat across from the student. 

“Ah… Hi…” Stiles suddenly felt underdressed in his holed sweater and beaten jeans. Raeken wore a crisp suit, his shoes were shiny and polished, hair well quaffed and arranged neatly on his handsome head, a large watch attached to his strong wrist. 

“I was worried you wouldn’t show.” Stiles said honestly, knee bouncing. Theo smiled blindingly “I would never stand you up, Stiles.” 

The boys heart skipped a beat for a moment. 

“Now.” Theo leaned back comfortably, fingers laced on the table in front of him “the terms of this job are simple. I will give you whatever you ask for the opportunity to be by your side, Stiles. I will not ask you to do anything you are uncomfortable with, all I need is a companion of sorts.” 

Stiles was surprised to say the least. “You mean you’re single?”

Theo laughed heartily again, embarrassment reddening on Stiles’ cheeks. He was always putting his foot in his mouth. “Don’t be surprised, Stiles. You’re a good natured man, honest, I like that.” The mans gaze felt heated to Stiles. “Of course it’s up to you. I’m more than willing to refer you to some good friends for work if you deny my proposition.” 

“No, I… I’ll do it… Uhm.” Stiles huffed, struggling to find words “Thank you… Mr. Raeken.”

“Please, call me Theo.”

They settled into a comfortable silence, Theo calling a sweet server for warm drinks and a variety of muffins. They ate, spoke, laughed, as if they’d known each other for years. 

“Are you two ready to pay?” Their server asked, sugar sweet and kind with the tray in hand “of course.” Theo gave her a charming grin while pulling out his wallet. Stiles went to do the same when he was stopped with a gentle hand “Stiles.” 

Their eyes met, Theo appeared serious and stern, as if Stiles pulling any cash from his pocket would be a federal offense. 

Stiles let him pay, pay for them both. “You didn’t have to…” “I did.” Theo gave him a sweet look “You’re my responsibility now, Stiles, your happiness and comfort is my priority.”

\------

“You what??”

Scott nearly dropped his dinner, mouth agape like a fish out of water. “Yeah, I couldn’t believe it myself at first.” Stiles said “But he paid for my food, my drink, even offered to drive me back to my apartment afterwards. He’s too good to be true.”

Derek stabbed at his noodles, looking angry and scandalised “I don’t trust him.” He said plainly, much like an overprotective sibling.

Stiles and Derek had dated in the past, although Derek had been a wonderful man and attentive lover they’d decided to go their separate ways. The other man had become a bit of a sibling for Stiles, much like Scott, protective and looking out for him as much as they could, including now.

“Can we at least meet this mysterious stranger?” Scott asked, stuffing his cheeks with sweet chicken. Stiles swirled his own herb noodles around his fork, staring into the cardboard box distractedly “yeah… I’ll ask him.” Scott seemed satisfied with that, although Derek stayed outwardly suspicious. 

Their night came to a conclusion after a shitty action movie and an irresponsible amount of cheap chinese food. Scott snored obnoxiously on the couch, limbs splayed out across the seat of the couch, leaving no room for anyone but himself. 

Derek had stalked off to the shower, leaving Stiles alone with his sleep talking best friend. 

Zzzzrp. Stiles’ phone vibrated against his hip, flip screen lighting up with a new message. 

**Unknown number**

_ Hello, dear.  _

Stiles committed to a staring contest with his phone for a few moments before typing out his own reply 

**To : Unknown number**

_ Who is this???? _

**From : Unknown number**

_ Theo, of course  _

Stiles quickly added the contact 

**To : Theo Raeken**

_ Oh hi!! Before I forget Scott and Derek wanted to meet you _

**From : Theo Raeken**

_ Sounds exciting _

**To : Theo Raeken**

_ Maybe we could meet tomorrow?? If you’re free  _

**From : Theo Raeken**

_ Of course, darling, i always have time for you _

Stiles felt his heart swell with the affection, he could practically hear Theos voice saying such nice things as if he were in the room.

They exchanged good nights, leaving Stiles with butterflies and anxiety swirling in his belly. 

\--------

When Theo arrived at Stiles’ apartment he looked incredibly out of place. He was dressed well, too well, to be in a shabby place like this, around college students barely making ends meet. 

“Theo, this is Scott - “ he presented “and Derek.” 

Theo gave his brightest smile, arm wrapped playfully around Stiles’ waist “It’s wonderful to meet you both.” He said, a hungry look in his eyes hugging the boy close. 

Scott placed both hands on his hips, taking a motherly role “what are your intentions with Stiles?!” He asked, Derek sitting broodily in the background 

“I want to take care of him.” Theo immediately replied. 

Scott nodded, thinking of his next question. “Is he like some kind of arm candy?! Are you a fucking pimp.” Scott began to get himself worked up, millions of horrible, terrible scenarios passing through his mind from simple heartbreak to an elaborate kidnapping with ties to the mob. 

Theo chuckled good naturedly, much to Stiles’ relief. “No, no, I’m CEO of a modest company, no shady business I promise you.” 

Despite the mans calm demeanor Stiles noticed his tight grip around his waist, Theos fingers twitching anxiously against his hip, as if he were nervous. Scott seemed to approve, Dereks permanent dark cloud somewhat dissipating. 

Stiles felt as if he were introducing his boyfriend to his parents, Derek and Scott asking him questions about his personal life, some a little TMI, others playful banter. Derek didn’t say much, as usual, but didn’t appear as if he were walking to his execution, which was a good sign. 

“I don’t think Derek likes me much.” Theo said, the two men now alone for the hour. “Don’t worry about him… He’s always kind of moody.” Stiles leaned against Theos side, both curled up on the patchy couch. “Truth me told I’ve never been so nervous in my life.” Theo said in his German sway, laughing all the while. Stiles appeared genuinely shocked “I never would’ve guessed.” 

They talked, Stiles found he enjoyed Theos company, he wasn’t overbearing or imposing. Stiles fell asleep by his side, slouched against the arm of the sofa, legs laying across Theos lap. 

He watched the young college student snore softly, his chin sunk into the boys chest in what looked to be an uncomfortable position. 

Perhaps Theo would call in sick tomorrow. 

\-----

Stiles’ situation has improved dramatically. 

Not only did he  _ finally  _ find a job, but Theo has been more than generous with gifts and donations. 

“Are you sure?” Stiles asked meekly, watching Theo drive. 

He’d been invited to spend the weekend with the man, “a friendly get together.” Theo had called it, “no funny business,”. 

“You know you’re no burden to me.” Theo said, one hand gripping the steering wheel, the other placed over Stiles’ own. “What should I tell Derek and Scott? I don’t know if they’ll approve of me staying over…” their presence was beginning to feel more and more parental, keeping a wary eye on Theo and his interactions. 

“I would rather you tell the truth but… Whatever makes you comfortable, Stiles, you know I’m not forcing you.” 

Stiles sat silently, cellphone in his free hand.

Maybe Derek and Scott didn’t need to know. Just this once. 

Theos home was immaculate. 

It was an average home, nothing too fancy, he lived just outside the city in the upper class suburbs, his home was surrounded with well tamed greens, one large tree in his front yard. 

Stiles carried his duffel bag up the stone steps leading to the black painted front door, following Theo. 

“It’s beautiful.” Stiles gasped, the inside was so  _ clean! _ No apartment could live up to this level of upkeep. “I’m glad you think so.” Theo grinned, looking flustered and embarrassed. 

Stiles gracelessly tossed his worn duffel onto a plush looking olive green sofa “I can take a couch.”

Theo appeared offended “No!” He nearly shouted, alarming Stiles “You can take my bedroom.”

Stiles flushed suddenly, images of sharing a bed with the handsome Theo Raeken were just too much for him. 

“I - uhm - are you sure? I mean…” Theo could feel Stiles’ jittery nervousness, his worries. Theo’s face softened with concern “I’m not going to impose on you, Stiles. You’re a beautiful young man, I only want you to be comfortable.” 

Stiles hummed softly, heart thrumming in his chest “honestly… I wouldn’t mind if we… y’know.” Stiles’ cheeks burned a hot pink, amusing Theo.

“I won’t push you… although my tastes are a little…. Unique.” 

Stiles found himself bound. His knees were comfortably held by the plush carpet of Theos bedroom, his wrists bound loosely behind his back. The man carefully fastened a collar around Stiles’ throat, tightening the leather just so. “Is it uncomfortable?” Theo asked, checking that the boy had breathing space.

“No… It’s fine.” Stiles murmured, his heart raced, what was Theo planning to do? 

“Now…. we need a safeword.” “Safeword?” “Something you say when you’re unhappy or uncomfortable.”

Stiles thought for a moment “Scott.” He said, nothing ruined a heated moment like thinking about Scott. Theo chuckled, agreeing. 

With two fingers curled around Stiles’ collar Theo pulled (dragged) him across the room. Stiles could visibly pinpoint when Theo shifted into character, his usually lax posture became rigid and stiff, his steps became heavy and purposed. 

Theo sat on the edge of his fresh smelling sheets, pulling Stiles between his legs. “Theo?” Stiles asked softly, body humming with mild anxiety. 

“Don’t speak.” Theo said sternly, unnaturally, tugging Stiles by the neck like a misbehaving dog. Theo pushed the pad of his thumb against Stiles’ lips, dragging the digit across his lower lip. 

Stiles followed the finger with his tongue, allowing Theo to push past his teeth to push his tongue against his fingers. 

“You’re a natural.” Theo whispered, his heated gaze felt like fire across Stiles’ nude body. 

Stiles wiggled to get closer, suckling on the tip of Theos thumb. The wet warmth of Stiles’ mouth sent sparks through Theos hips and legs, he could feel his cock already hardening in his pants. 

“Such a good boy.” He whispered, using his free hand to free his dick. 

Stiles startled at the sight, stomach clenching in knots. “You ever sucked one, before?” Theo asked, an unfamiliar smirk on his handsome face “Uhm…. yeah.” Stiles avoided direct eye contact with the mans veiny cock, cheeks hot. 

The warm skin gently slapped against Stiles’ cheek, Theo pushing the head against Stiles’ lips. He opened up, allowing Theo to push himself into Stiles’ mouth, the bulbous head nearly hitting the back of his throat. “Show me how good you are.” Theo cupped the back of Stiles’ head, setting a steady pace with a tight grip on Stiles’ short locks. 

Stiles kept his eyes clench shut, Theo using Stiles’ mouth as some sort of pleasure vessel. The lock, thick rod pushed past Stiles’ tonsils and down his throat, the wet flesh constricted around Theo’s cock as the boy attempted not to gag. 

Theo groaned loudly, pushing his hips forward towards the source of the wet heat. Stiles let out a muffled sound of protest, he felt a thin sheet of sweat forming on his body, a startling spark of excitement shot through Stiles’ body. 

He’d never been used like this before, Derek had been a compassionate lover, always asking if Stiles was alright, making sure he was never uncomfortable or unsatisfied. 

Stiles felt like a slut, like some sort of cum dumpster for Theo Raeken. 

He  _ liked  _ it.

Theos grunts became louder, his broad chest heaving as his hips stuttered. With a drawn out sigh Theo came down Stiles’ throat, a searing gush of fluid filled Stiles’ mouth like thick cream, released when Theo pulled out from his lips. 

Stiles struggled to swallow all of Theos cum, some white spilling down his chin and staining his cheeks. He heaved, struggling to breathe after being used. 

“Such an excellent mouth.” Theo growled, hand still hooked tightly in Stiles’ hair “Come up on the bed, boy, let me take care of you.” 

Stiles stood with a wobble, reminded of his arms resting against his tailbone, the loose cord just enough to allow him to rest his shoulders. 

Theo cupped the boys erection, massaging his balls gently “naughty mutt, you like being my cum bucket?” He hissed into Stiles’ ear, hot breath fanning across Stiles’ skin like flame. Stiles whimpered, rump pressed against Theos somewhat softened dick, back pressed against his still clothed chest, legs spread shamelessly. 

“Answer me.” Theo growled dangerously, violently tugging Stiles’ head back to expose his throat. 

“A-ah -! Yes.” Stiles cried, cock twitching. A hot palm slid across Stiles’ skinny thigh, inching horribly closer to his hard on. “I’d love to cover you in my cum.” Theo sighed softly, gripping Stiles’ aching dick “you’d smell like me - like my jizz - constantly. You’d be  _ mine _ .” Stiles moaned loudly, precum oozing from his slit like the tears in his eyes. 

Stiles felt Theos cock hardening against his tailbone, poking him. “My little whore. You want my dick, don’t you? You’d beg for it, on your knees like some sort of lowlife slut.” Theo tugged Stiles’ hair once more, igniting a pained whimper from the boy. He sped the tugging motion on Stiles’ dick for only a moment before returning to an agonizingly slow pace, not nearly enough to satisfy him. 

“I - I wanna be… your slut.” Stiles mewled, hips humping into the air for more friction. Theo moaned loudly, mouth attaching itself to the boys pale neck just under his ear. Theo nibbled and bit at Stiles’ taut throat, licking against his jaw. Theo stroke the cock in his hand with vigor, Stiles’ moans becoming higher and higher as his orgasm approached. 

“You gonna cum?” Theo hissed, gripping the base and head of the boys cock, thumbing his slit, electrifying his balls. “Fuck - fuck-fu-!!” Stiles shrieked, semen finally spurting from his dick on to his chest and the bed sheets. 

Theo suckled at the boys shoulder, leaving multiple darkening hickies in his wake “are you alright?” Theo asked, immediately switching back to the kind persona Stiles knew. With well practiced hands he released Stiles’ once bound wrists, swiftly removing the leather collar from around the boys throat. “Yeah.” Stiles said, eyes heavy with exhaustion “That was… crazy.” He laughed, leaning against the other mans solid form. “You did wonderfully.” Theo cooed, pressing an affectionate smooch against the boys warm cheek, strong arms holding him like a vice. Stiles felt warm, safe in Theos embrace, he knew Theo would never hurt him. 

\-----

“Where were you?!” Scott shrieked in a motherly manner, Monday had finally arrived, time for Stiles to return to his job and college classes, not to mention back to Derek and Scotts overprotective ways. 

“Nowhere.” Stiles insisted, taking the massive bouquet of lavender flowers and placing them delicately into an equally pastel blue vase. Theo had gifted Stiles the plants as he left the mans home  _ “They’re nearly as lovely as you are.”  _ He’d said, hand lingering over Stiles’ own. 

“Uh huh.” Scott’s eyes narrowed in suspicion “and where, pray tell, did those HICKIES come from?” He hissed, glaring daggers at the purple and yellow bruises on Stiles’ throat and shoulder. 

Stiles was caught, he knew. “I…. spent the weekend with Theo.” 

Scott nearly had a heart attack, releasing a very very unnatural sound of distress. “You fucked! You totally fucked, didn’t you?!” He shouted a bit too loudly, Stiles scolded him with a brotherly shove “Shut up!” He shouted/whispered.

“Stiles you know I don’t trust him!” Scott said harshly, strong hand gripping Stiles’ forearm a little too tightly. “But I do!” Stiles replied, wincing “He’s your fucking pimp. Like some sort of sugar daddy.” Scott scoffed “Did he pay you to lay on your back or some shit?” 

A loud WHACK sounded through the apartment kitchen, a bright red mark blooming on Scotts cheek. “Fuck you, Scott.” Stiles’ voice wavered, warm tears flooding his eyes. Scotts once mocking expression vanished, replaced with regret. Before another word could be uttered Stiles stormed out of his own apartment, viciously slamming the door behind him. 

\----

“Good morning, Ms. Stewart.” Theo walked briskly past his secretary, making a bee-line for his office. 

“Hold on a moment, Theo.” he stopped in his tracks, dread hanging over him like a dark storm cloud “You had an appointment over the weekend, I called you a million times. What were you doing?!” She sounded upset although Theo kept his back turned to her “Personal business.” He answered flatly, hurrying off to his office despite Tracys objections. 

Memories of nights with Stiles flashed through Theos mind, struggling to complete his work and reschedule missed appointments. “ _ Mr. Raeken? _ ” The mans voice crackled through the phone receiver “oh - sorry, what?” Theo snapped out of his day dreams, searching through piles and piles of documents “ _ I SAID - _ ” Theo immediately lost interest, pen scribbling down mindless words and phrases, responding with a “yeah” or “uh huh” to the man on the telephone.  

Tracy smiled sweetly as she hung up the desks telephone, one hand scribbling notes and using the other to type notes into the company's computer. “Uhm… Excuse me.” A young mans voice disturbed Tracy from her working trance, he was a sweet looking young boy, short brown hair and doe eyes. Black and blue marks lined his shoulders and neck, hickies no doubt. 

“Yes, how can I help you?” Tracy allowed her voice to sound shrill and inviting, although to Stiles it seemed more like claws on a chalkboard. 

“Uhm, I was hoping maybe I could talk to Theo Raeken. I’m… a friend.” Stiles fiddled nervously with his thumbs, struggling to make eye contact with the woman. 

Dread filled Tracys stomach. Was Theo sleeping around with college students now?!? 

“Of course. Follow me.” Her smile became grim and forced, even outwardly noticeable to Stiles, the click of her sleek polished heels sounded more like the ruthless pounding of giants feet. 

“Theo, you have a visitor.” Tracy pulled Theo from his working riveree, the man kept his eyes downcast to the desk papers, distractedly ordering her to allow entry. Stiles felt the sharp, angry stare like daggers in his back when walking past Ms. Stewart, setting him somewhat on edge. 

“Stiles!” Theo immediately perked like a puppy seeing their owner after a long day “what a surprise. Did you need something?” Theo stood from behind his desk, approaching the boy with open arms. 

Stiles allowed himself to be held by him, all the worries and anxieties came rushing back like a drowning ocean. Tears overflowed from his eyes, Stiles making a strange squeak of despair. 

“What’s wrong?” Theos voice sounded muffled to his ears, the mans large arms encasing the boy. “Scott….” Stiles sniffed loudly, wiping his tears in Theos crisp button shirt. 

“He just… Said some terrible things. I just…. Need to be with you. Right now.” He felt childish and sad, he wanted reassurance that this isnt’ some sort of game to Theo. That maybe he was serious about Stiles. 

“Of course.” Theo spoke softly, pressing his nose into Stiles’ hair “do you want to leave? My home isn’t far from here.” 

Feeling somewhat selfish Stiles pulled Theo away from his work, following the somewhat older man through the massive sleek office building. “Good afternoon, Ms. Stewart.” Theo waved dismissively, one hand latched onto Siles’. 

-

_ “How do you feel about skirts?” Stiles was startled by the question, sitting silently with twiddled thumbs on Theos bedspread. “Oh, uhm… They’re okay I s’pose.” He answered “I’ve never worn one before.” Theo gave Stiles a warming and understanding smile, pulling a purple shopping bag with curved writing from the back of his closet “I have a gift for you, if you’ll take it.”  _

Now Stiles found himself in Theo Raekens lavish bathroom, pulling and tugging at the flowy fabric of a white sunday skirt Theo had purchased. 

The panties that came standard were somewhat tight around the students behind, hugging just a bit too tightly. 

“Are you alright?” Theo called from his attached bedroom, knocking the white door just twice. Stiles called back ‘yes’, mentally preparing to step out in front of the CEO. 

“You look beautiful.” Theo held Stiles by the hips, smile broad. The students cheeks felt hot, the lush skirt brushing intimately against his bare thighs “You really think so?” He mumbled 

Theo hummed in affirmative, playfully pulling the thin skirt higher towards the boys hip, exposing the lace of his panty. 

“Gorgeous.” Theo had that look, the heated gaze and dark character. Thick fingers slipped between the strip of white and Stiles’ skin, massaging the skin of his hip and thigh. 

Stiles mewled, allowing Theo to pull his sleek calf up to the mans clothed hip, holding it with a firm grip. “You’d make an amazing wife.” Theo hissed, grinding dangerously against him. 

Stiles felt pliant in the mans arms, skin buzzing with arousal and excitement. 

He felt daring, Stiles wanted to push his dominant partner just a bit. He bit Theo, teeth sinking into the mans neck and creating deep suction. Carefully whittling at the spot Stiles detached when he felt confident he’d left a mark. Theos body was rigid, his already hard grip on Stiles’ leg became bruising and harsh. Stiles nearly regretted his decision. 

“Such a bad boy.” Theo growled, violently throwing Stiles do the bed, watching him bounce.

“Are you looking for punishment?” Stiles nearly didn’t recognize Theo, his face, handsome as it were, was dark and possessive like a Jekyll and Hyde situation. A sharp shock of arousal and fear shot through Stiles at that moment, his whole body trembled in anxiety and want. 

“Please.” Stiles moaned, his face immediately came in contact with Theos soft pillows, the older man positioning his ass in the air. 

The delicate skirt was shoved down to Stiles’ arched back, exposing his ass spilling from the too tight underwear. “Such a slut.” Theo hissed, pulling the unfit fabric to slap back against the boys behind. 

Stiles breathing became heavy and labored, squirming under Theos intense stare. 

A sudden, unexpected slap shocked the student, a surprise whimper coming from his throat. “Count.” Theo demanded, voice deep and husky. 

Stiles did as asked, slim fingers gripping the fat pillows for leverage. 

_ SMACK  _ “o-one.”

_ SMACK!  _ “Two-!”

_ SMACK SMACK _ “three - four.” 

_ SMACK  _ “fi-uh-ve!” 

Stiles struggled to concentrate on the numbers, occasionally missing one or two in the painful sensation of the spanking. His rump was a fiery red under Theos palm, heat radiating from the skin. 

“You’re being so good now.” Theo praised, thumbs spreading the boys cheeks, the lace fabric of his panties causing friction against his hole. Stiles moaned at the rough treatment, wiggling his behind to entice Theo. 

He chuckled lovingly, gently sliding the boys underwear to his ankles “you want my cock?” Theo growled, slicking himself. Stiles moaned a genuine ‘please’, cock twitching against his belly. 

Their fuck was quick, and emotional at least for Stiles. 

He felt ravished, Theo kept his head tucked against the junction of Stiles’ neck and shoulder, hot mouth pressed against the students skin like lava. Skirt hiked up to his stomach Stiles’ legs were thrown in the air on Theos thighs. 

Stiles could hardly control his voice, his moans and cries felt desperate, his fingers were tightly gripped in Theos dark hair like reins. 

“Th-Theo I - wanted to… ask you something.” Stiles grunted beneath him, body maneuvered to sit up, arms and legs tightly bound around Theo like an octopus while the CEO bucked upwards into his entrance “not now.” Theo hissed, hands hidden beneath Stiles’ skirt fingers tracing his stretched hole. “B-but - oh!” Stiles squealed, liquid heat filled his hole like lava. 

Tossed to the bed, legs hoisted high above his head Stiles struggled to speak “I-I really need to - talk to - you!” Stiles moaned in surprise when a wet tongue lapped away at the semen that managed to escape his hole, Theo held both of his legs to keep them spread to accommodate him. 

The sensation left him when Theo pulled away “sit on my face.” He commanded, already shuffling the younger man above his face, hands holding his hips still while pushing the tip of his tongue against Stiles’ hole. 

“Ah -ahhh!” The student moaned, the mans muscle slowly licking out his own cum. Stiles squirmed, taking hold of his own cock to speed his orgasm. 

Theos own dick was making valiant efforts to harden again, twitching against his thigh with the taste of the boy above him. Writhing in pleasure Stiles finally came, small spurts of white shot from his tip landing on the bed and Theo. 

“I… I came.” He huffed, trembling above the other mans face. Theo finally detached himself from Stiles’ hole, giving warm kisses to the boys hips.

\---

“I want to talk to you.” Stiles demanded, curled against the mans side, Theos arm encasing him comfortably. “Alright.” He sighed in defeat “what’s bothering you?” 

“I want to know what we are. Like, what is our relationship? Scott called you a… sugar daddy.” Stiles felt somewhat ashamed, embarrassed, like Theo would be upset for asking such questions. 

“Do you want to be my partner?” Theo asked, rolling his body to face the other man “You’re wonderful Stiles. I would be honored to love you.” Stiles’ heart drummed against his rib cage, his palms became wet and clammy with anxiety “Yeah. That would be nice…” 

They kissed, Theo hauling himself above the student to lock lips, their tongues intertwined like snakes. 

\----

“I’m dating Theo now. It’s official.” Stiles announced, struggling to meet Scotts gaze.

“That’s great.” Derek said, half distracted by the paperback novel in his hand. Scott looked guilty, brow creased “That’s awesome man but... “ 

“But nothing!” Stiles nearly shouted “I’m an adult, you should respect by decision even if you don’t - “ Scott interrupted his friend, shoving Stiles’ shoulder dismissively “I wanted to apologize!” 

Derek watched the two men with bland curiousity, face neutral. “I’m sorry, dude. I said some fucked up shit and just…. I want you to forgive me. Please?” Scott shuffled awkwardly, leaning back on the overstuffed sofa in the apartment “Yeah, man… Of course!!” Stiles beamed like the sun, the two engaging in a ‘bro hug’. 

“But seriously though.” Scott deadpanned, arms full of Stiles “Say the word and I’ll kick his ass.” 

\--

“Theo.” Tracy Stewart approached the CEO, Theo stood unwittingly with shitty brewed coffee in his hand (the machine was really getting on in years now) when the woman wormed to his side, long nails scratching at his arm like a cat “Hello, Ms. Stewart.” Theo hissed, chills running up his spine (and not the good kind) 

“I was wondering if you were free tonight.” She said, pressing her chest against his side in an obvious flirtatious move. “Well, I -” a loud ring interrupted their conversation, Theo waved half heartedly to Tracy when he fished out his cellphone, the screen lit with the name STILES with little emoji hearts next to it (courtesy of yours truly.) 

**FROM : STILES ❤❤❤**

_ Hey boo ;) _

Theo chuckled

**TO : STILES ❤❤❤**

_ Hello, dear. _

**FROM : STILES ❤❤❤**

_ We still on for tonight?? I got a surprise for u ;) _

_ \---PICTURE ATTACHED--- _

Theo knew better than to open the image with Tracy by his side, despite the temptation to do so. He grinned to the woman, knowing she could read the texts aswell 

**TO : STILES ❤❤❤**

_ Now now baby I’m at work _

_ I’ll see you tonight _

**FROM : STILES ❤❤❤**

_ Fuck me silly  _

_ Xxx _

“Sorry, Ms. Stewart.” Theo laughed, tucking the cellphone away in his slacks pocket “I’m busy.” 


End file.
